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Acceleration of Acetal Hydrolysis by Remote Alkoxy Groups: Evidence for Electrostatic Effects on the Formation of Oxocarbenium Ions |
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| Authors: | Dr. Angie Garcia Douglas A. L. Otte Dr. Walter A. Salamant Jillian R. Sanzone Prof. K. A. Woerpel |
| Affiliation: | 1. Department of Chemistry, New York University, 100 Washington Square East, New York, NY 10003 (USA);2. Bridgestone Americas Center for Research and Technology, 1659 S Main St., Akron, OH 44301 (USA) |
| Abstract: | In contrast to observations with carbohydrates, experiments with 4‐alkoxy‐substituted acetals indicate that an alkoxy group can accelerate acetal hydrolysis by up to 20‐fold compared to substrates without an alkoxy group. The acceleration of ionization in more flexible acetals can be up to 200‐fold when compensated for inductive effects. |
| Keywords: | carbocations carbohydrates electrostatic effects hydrolysis kinetics |